Playback error - An error occurred loading items to play

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So on my Mac lots of media has stopped playing that used to work just fine. And I keep getting the playback error: An error occurred loading items to play.

It seems to be mostly with shorter tv length media. Movies mostly seem to work fine. All the files play fine on my Nvidia shield plex. But when I try to watch on my macbook, those files wont play? It just stopped working all of the sudden!

Help!

Server Version#: Version 1.18.7.2457
Player Version#: Version 4.22.2

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If I move my media drive to my mac. and run my media server from there, the problem goes away. But I dont want to do that. So why does it fail when streaming?

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